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Issue 20, 2020
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Spirodesertols A and B, two highly modified spirocyclic diterpenoids with an unprecedented 6-isopropyl-3H-spiro[benzofuran-2,1′-cyclohexane] motif from Salvia deserta

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Abstract

Two highly modified spirocyclic diterpenoids with an unprecedented 6-isopropyl-3H-spiro[benzofuran-2,1′-cyclohexane] motif, spirodesertols A (1) and B (2), four new icetexane diterpenoids, salviadenones A–D (3–6), together with their biogenetic precursor, 20-deoxocarnosol (7), were isolated from the root extract of Salvia deserta. Their structures were elucidated by spectroscopic analysis, quantum chemical calculations including the 13C chemical shift calculations with DP4+ probability analysis and electronic circular dichroism (ECD) calculations, and single-crystal X-ray diffraction analysis. The plausible biogenetic pathways for 1–6 were proposed. Compounds 1–7 were evaluated for their cytotoxicity against five cancer cell lines. Spirodesertol A (1) showed more potent cytotoxicity against the A-549, SMMC-7721, and MCF-7 cancer cell lines than the positive control, cisplatin.

Graphical abstract: Spirodesertols A and B, two highly modified spirocyclic diterpenoids with an unprecedented 6-isopropyl-3H-spiro[benzofuran-2,1′-cyclohexane] motif from Salvia deserta

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Article information


Submitted
19 Jun 2020
Accepted
30 Jul 2020
First published
31 Jul 2020

Org. Chem. Front., 2020,7, 3137-3145
Article type
Research Article

Spirodesertols A and B, two highly modified spirocyclic diterpenoids with an unprecedented 6-isopropyl-3H-spiro[benzofuran-2,1′-cyclohexane] motif from Salvia deserta

G. Zheng, A. Kadir, X. Zheng, P. Jin, J. Liu, M. Maiwulanjiang, G. Yao and H. A. Aisa, Org. Chem. Front., 2020, 7, 3137
DOI: 10.1039/D0QO00735H

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